Side chain hydroxylation of aromatic compounds by fungi. Part 4. Influence of the para substituent on kinetic isotope effects during benzylic hydroxylation by Mortierella isabellina
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 10,p. 1651-1655
- https://doi.org/10.1039/p29900001651
Abstract
The benzylic hydroxylation of a series of para-substituted toluenes by the fungus Mortierella isabellina has been studied by using CD3, CHD2, and CH2D methyl labelled substrates. Inter- and intra-molecular primary and secondary deuterium kinetic isotope effect ratios have been determined: the intermolecular primary effects are maximal with strongly electron-withdrawing para substituents (R = CN and CF3), while the intramolecular primary effects are minimal for R = H but increase in instances where R is electron donating or withdrawing. These results are interpreted in terms of a dependence of the hydroxylation mechanism on the nature of the para substituent.Keywords
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